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Abstract

In the title crystal structure, C13H9N4+·ClO4−·H2O, cations, anions and water mol­ecules are linked through inter­molecular N—HO, O—HN and O—HO hydrogen bonds, forming layers parallel to (001). In addition, there are weak π–π stacking inter­actions between the layers, involving the cations and with centroid–centroid distances in the range 3.584 (2)–3.662 (2) Å, forming a three-dimensional network.

Related literature

For background to 1H-imidazo[4,5-f][1,10]-phenanthroline and its use as a mol­ecular building block, see: Xiong et al. (1999); Yu et al. (2009); Liu et al. (2009).

Acknowledgments

The author is grateful to the Zhejiang Economic and Trade Polytechnic for financial support.

supplementary crystallographic
information

Comment

1H-imidazo[4,5-f][1,10]-phenanthroline (IP) is
an important derivative of 1,10-phenanthroline
that has been used to recognize the
secondary structure of DNA in an
Ru(II) complex (Xiong et al., 1999).
IP is a good molecular building block
and has been used to construct some
interesting structures
(Yu et al., 2009, Liu et al., 2009).
In an attempt to form a Zn(II) complex with IP,
we adventitiously formed the title compound (I) and its
crystal structure is determined herein.

The asymmetric unit of (I) is shown in Fig 1.
In the crystal structure N-H···O, O-H···N and O-H···O
hydrogen bonds link cations, water molecules and perchlorate
anions into a 2-D network (Fig. 2). Details of the
hydrogen-bonding geometry are given in Table 1.
In addition, there are weak π–π stacking interactions between
layers, involving cations with centroid to centroid distances in
the range 3.584 (2)-3.662 (2)Å forming a three-dimensional network.

Experimental

IP (0.23 mg,0.1 mmol), Zn(ClO4)2 (0.27 mg,
0.1 mmol), were dissolved in methanol. The mixture
was heated and stirred for ten hours under reflux.
The resulting solid was then
filtered off to give a pure solution which was treated with
diethyl ether in a closed vessel.
Five weeks later, single crystals were obtained.

Refinement

All H atoms were visible in difference Fourier maps but were subsequently
placed in calculated positions treated as riding with C—H = 0.93,
N—H == 0.86Å and with Uiso(H) = 1.2Ueq(C,N). The H atoms of the
water molecules were included in the
subsequent refinement with O-H = 0.84Å and Uiso(H) = 1.5Ueq(O).

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F2, conventional R-factors R are based
on F, with F set to zero for negative F2. The threshold expression of
F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F2 are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.